反応 #2200581

反応方程式

TEMPO

(2R,3S)-2-methyl-3-tetrahydropyranyloxybutanol

NaOCl

NaHCO3

sodium bromide

→

aldehyde

収率 92.3%

(2S,3S)-2-methyl-3-tetrahydropyranyloxybutyraldehyde

収率 92.3%

溶媒

toluene

EtOAc

H2O

反応条件

後処理

1. 1
   その他The aqueous phase was separated
2. 2
   洗浄washed with Et2O (50 ml)
3. 3
   洗浄The combined organic phases were washed with a KI solution (80 mg)
4. 4
   workup.DISSOLUTIONdissolved in aqueous 10% KHSO4 (20 ml)
5. 5
   乾燥with a 10% aqueous sodium thiosulfate solution (10 ml), brine (20 ml), and dried (MgSO4)
6. 6
   ろ過Filtration and concentration under vacuum

実験手順

An aqueous NaOCl solution (11 mmol, 5.3 ml of a 12.5% solution) and NaHCO3 (2.43 g, 29 mmol) was added dropwise, over a period of 1 hour, to a cold (0° C.), rapidly stirred (>1000 rpm), biphasic mixture consisting of (2R,3S)-2-methyl-3-tetrahydropyranyloxybutanol (5) (1.88 g, 10 mmol), TEMPO with free radicals (31.25 mg, 2%), sodium bromide (1.029 g, 10 mmol), toluene (30 ml), EtOAc (30 ml) and H2O (5 ml). The aqueous phase was separated and washed with Et2O (50 ml). The combined organic phases were washed with a KI solution (80 mg) dissolved in aqueous 10% KHSO4 (20 ml), and then with a 10% aqueous sodium thiosulfate solution (10 ml), brine (20 ml), and dried (MgSO4). Filtration and concentration under vacuum gave the desired aldehyde 6 (1.72 g, 92%) which was used for the next reactions without further purification.

出典